Cadey O'Leary Collection

What is the right approach to listing your home?

The one that prioritizes 𝒚𝒐𝒖𝒓 interests, objectives and ultimately delivers the best outcome possible.
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Over the next week, we'll close two very different properties.
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📍1721 Fern was sold off-market. Our clients valued privacy and discretion, so rather than relying on broad exposure, we focused on telling the story of their home, capturing the lifestyle it offered and connecting with the right audience. The result was multiple offers and an outcome that reflected both the uniqueness of the property and what mattered most to our sellers.
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📍1313 Ritchie called for a different approach. Buyers in this market are actively watching new inventory and working closely with agents, so reaching the broadest pool of qualified buyers was our priority. We brought the home to market quickly, created momentum through frequent, dedicated showing windows and a strong digital presence, maximizing visibility from day one.
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Every home has a story and every seller has a different set of priorities. Our job is to build a winning strategy around both.

The most memorable homes are often expressions of the people who create them. Some take shape through gardens and landscape, others through architecture, art or the thoughtful adaptation of space. In celebration of this weekend’s Old Town Art Fair and Garden Walk, we explore four distinctive properties where creativity has left a lasting imprint, revealing the many ways beauty can be woven into everyday living.
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From a garden retreat tucked within the Old Town Triangle Historic District to a rare double-lot residence devoted to outdoor living, a reimagined live/work space designed for creative expression and an estate where sculpture and landscape share equal billing, each offers its own interpretation of living well.
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A look at what happens when personality leaves its mark on a place.

Read more ➡️ https://bit.ly/4e6YLvl⁣
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📍𝟏𝟕𝟓𝟓 𝐍 𝐌𝐨𝐡𝐚𝐰𝐤
6 bed 5.1 bath
Offered at $5,495,000
Listed by Natasha Motev with Jameson Sotheby's⁣
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📍𝟏𝟗𝟎𝟔 𝐍 𝐅𝐞𝐫𝐧
3 bed 2.1 bath
Offered at $1,750,000
Listed by James Buczynski with Compass⁣
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📍𝟓𝟕𝟕𝟏 𝐒𝐖 𝟗𝟒𝐭𝐡, 𝐏𝐢𝐧𝐞𝐜𝐫𝐞𝐬𝐭, 𝐅𝐋
8 bed 7.2 bath
Offered at $22,500,000
Listed by The Jills Zeder Group with Coldwell Banker⁣
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📍𝟐𝟑𝟑𝟏 𝐍 𝐄𝐥𝐬𝐨𝐧
2 bed 2 bath
Offered at $1,299,900
Listed by Shawn Nam with Fulton Grace Realty

𝐂𝐎𝐌𝐈𝐍𝐆 𝐒𝐎𝐎𝐍

The kitchen sold us on this one.

An oversized island, custom Italian cabinetry, Viking appliances and a Thermador double oven, all wrapped in natural light from floor-to-ceiling windows with south and west exposures.

Then there’s the neighborhood: Sunday mornings at the Farmers Market, dinner at Club Lucky and evening walks on the 606, all just a few blocks away.

Direct elevator entry, two private outdoor spaces and two garage parking spots round out this Bucktown home.

📍1611 N Hermitage
3 bed | 2 bath

DM us for a first look.

Over the past month, we have hosted client gatherings, attended charity events, enjoyed musical performances and a serendipitous connection.

Last week, I had the pleasure of meeting the author of 𝑨 𝑳𝒊𝒕𝒕𝒍𝒆 𝑴𝒐𝒓𝒆 𝑺𝒐𝒄𝒊𝒂𝒍, a new book that explores the unexpected benefits of leaning in more and engaging with others. Nicholas Epley is a professor at Chicago Booth and researcher who integrates empirical data with anecdotal discoveries in this fascinating book. The black and white photo of the two of us was taken shortly after we discovered that my brother interviewed him the week prior on his podcast, John O'Leary - Live Inspired.

A wonderful, memorable moment that reinforces his book’s premise. Something I am working to expand upon.

This season has been defined by highly nuanced conditions across every segment of the market, resulting in $16 million in closed and pending sales this spring, with 40% of our transactions never hitting the MLS.

We have approached each client and property with a personally tailored strategy designed around their unique circumstances and timelines while pursuing winning outcomes.

These sales have been achieved through a thoughtful mix of Private Network listings, strategic MLS exposure, customized marketing plans, agent-to-agent outreach and priority access to off-market opportunities.

Relationships, expertise and results.

In today’s market of change and industry disruption, planning, knowledge and access are more important than ever. We are here to be of help and delighted to be a resource

Coming soon along the edge of Lincoln Park and Lakeview, this three-bedroom penthouse offers the best of North Side living with a wider floor plan, beautiful natural light and three private outdoor spaces.

Gracious interiors feature soaring ceilings, elegant millwork, custom-stained hardwood floors and a beautifully appointed chef’s kitchen, all designed for both easy everyday living and entertaining.

Above it all, a 1,700 sqft rooftop terrace delivers sweeping neighborhood and skyline views.

📍𝟐𝟗𝟏𝟖 𝐍 𝐒𝐡𝐞𝐟𝐟𝐢𝐞𝐥𝐝, 𝟒𝐒
3 bed | 2 bath
Offered at $950,000

𝐏𝐫𝐞-𝐦𝐚𝐫𝐤𝐞𝐭 𝐨𝐩𝐞𝐧 𝐡𝐨𝐮𝐬𝐞:
Friday | 4-6pm
Saturday | 12-1:30pm

DM for more information or to schedule a private tour.

The market is highly nuanced right now.

What we’re seeing in Lincoln Park is very different from what’s happening in the South Loop, especially in the $1M+ condo market.

In Lincoln Park, inventory has tightened to just 1.3 months of supply and well-positioned homes are moving quickly.

Meanwhile, the South Loop luxury market is sitting closer to 4 months of supply with homes taking 60 days or longer to sell, often with price adjustments before doing so.

A reminder that broad market headlines only tell part of the story. Neighborhood, property type and buyer behavior matter more than ever.